Triethylamine → HCID 178481845, compound

HRID 1276123Notes

Reaction equation

HRID 1276123 reaction equation
[Cl:1][C:2]1[C:10]([C:11]([NH:13][C:14]([CH3:18])([CH3:17])[CH2:15]Cl)=[O:12])=[C:9]([S:19]([CH3:22])(=[O:21])=[O:20])[CH:8]=[CH:7][C:3]=1[C:4](Cl)=[O:5].C(N(CC)CC)C.[OH:30][C:31]1[N:35]([CH3:36])[N:34]=[CH:33][CH:32]=1>O1CCOCC1>[Cl:1][C:2]1[C:10]([C:11]2[O:12][CH2:15][C:14]([CH3:18])([CH3:17])[N:13]=2)=[C:9]([S:19]([CH3:22])(=[O:21])=[O:20])[CH:8]=[CH:7][C:3]=1[C:4]([C:32]1[CH:33]=[N:34][N:35]([CH3:36])[C:31]=1[OH:30])=[O:5]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 53932118HCID 53932118, compoundHCID 178481816HCID 178481816, compound

Product 1

HCID 178481845HCID 178481845, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent3×

Procedure

At 15° C., 1.65 g (4.3 mmol) of 2-chloro-3-(1-chloro-2,2-dimethyleth-2-ylaminocarbonyl)-4-methylsulfonylbenzoyl chloride in 25 ml of dioxane and 0.45 g (4.5 mmol) of triethylamine in 10 ml of dioxane were added dropwise to a mixture of 0.42 g (4.3 mmol) of 5-hydroxy-1-methylpyrazole in 10 ml of dioxane. The mixture was stirred at room temperature for 4 hours and then filtered off through silica gel, which was rinsed with dioxane. The combined filtrates were concentrated to 60 ml and admixed with 1.24 g (9 mmol) of finely powdered potassium carbonate. The mixture was heated under reflux for 5 hours and cooled, the solvent was removed under reduced pressure, the residue was taken up in water, insoluble components were filtered off and the solution was acidified using 10% strength hydrochloric acid and extracted repeatedly with ethyl acetate. The combined organic phases were subsequently washed with water, dried and concentrated. 1.2 g (68% of theory) of 4-[2-chloro-3-(4,4-dimethyl-4,5-dihydrooxazol-2-yl)-4-methylsulfonylbenzoyl]-5-hydroxy-1-methyl-1H-pyrazole were obtained.

Workup

  1. filtrationfiltered off through silica gel, which
  2. washwas rinsed with dioxane
  3. concentrationThe combined filtrates were concentrated to 60 ml
  4. temperatureThe mixture was heated
  5. temperatureunder reflux for 5 hours
  6. temperaturecooled
  7. customthe solvent was removed under reduced pressure
  8. filtrationinsoluble components were filtered off
  9. extractionextracted repeatedly with ethyl acetate
  10. washThe combined organic phases were subsequently washed with water
  11. customdried
  12. concentrationconcentrated

Sources & evidence

ORD record
ord-850e494add9f4c2ba57da9f91b2993fb
Source dataset
uspto-grants-2000_12
Patent number
US06165944

Reaction notes

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